Rebekah Roque
Sep 4, 2018 · 5 min read

Working Hard, Working Smart, and the Pitfalls in Between

It was a Friday night and all I could think of was how to make a quick escape from the office to get my whiskey fix. A welcome drink to my body that has known caffeine all week. My team has surely been thinking the same — escaping. At this point, I wasn’t sure anymore what fuel we were running on. Bad coffee? Pep talks thinly veiled as reprimands? A raise?

One thing was certain though and that was exhaustion. We were all spent from a week’s worth of meeting deadlines that didn’t seem to end. There’s neither energy nor banter left in any of us, except when rounds were made to check on updates. Occasionally, a loud snore would be heard across the room.

We were nowhere near the end goal. Everybody knew that. But our top executives insisted that we make a go for it because it was our clients first time to do business with us. We had to get our foot in the door.

“Yeah, sure. We’ll get you the revisions first thing tomorrow morning. We have a lot of rockstars in our team who can make that happen,” said our CEO often.

Nice to bask in that word, rockstar. But assigning rockstar status is a mere deflection to a much needed organizational introspection.

The work hard vs work smart debate has taken up so much conversation space in recent years. Admittedly, I have never given it much thought until I stumbled upon a Twitter exchange between tech giants classifying others, or themselves, as proponents to either the work hard or work smart school of thought. To which I often floundered, not knowing whether to advocate one over the other.

Beause even as I drove myself to exhaustion, I understood where the need was coming from.

Circumstances are often delicate in a startup ecosystem and it takes meaningful experience to know when to work hard or when to work smart or when to do both. It cannot be constrained in a binary debate. Doing so would assume mutual exclusivity, restricting us to choose one over the other. For why can’t a hardworking individual also be a smart-working one? It also begs a second problematic assumption. We measure both in terms of hours clocked in. One can work tirelessly for 12 hours but can accomplish twice the productivity of what would otherwise have been a 24-hr workload. Does working smart mean sticking to a strict 8-hr routine? Why not 6? Or why not 10 hours split effectively throughout the day?

Hard work has a bad reputation these days. It is often an image of an individual from older generations who refuse the currency of the new blood: automation and technology. In my case — in my defense, really — I was young and a neophyte in the field. I was not in a position to negotiate, let alone push back. In a bid to gain experience, I said yes to whatever was thrown my way. And all the mistakes were eventually paid for in long irregular work shifts.

So I get it. Hard work is a novice’s ally. I see it among those who venture out in their first steps with neither help nor privilege but only sheer determination
to create something. This is dignified hard work, the virtue we often praise. But things can get muddled and what is once a virtue can quickly become vice.

There is hard work driven by greed, others use it as an existential reassurance. “There’s an endless list of things to do so I must be valuable!” But most commonly, it is a byproduct of lapses in communication and a misguided vision.

When a person has put in the time to get a project done, as a manager you respond with gratitude. This person has, in all likelihood, abandoned other responsibilities and so a sincere thank you is the least he gets. You give him a pat on the back and make him feel valuable. But this also leaves little wiggle room for criticism without sounding unappreciative. It takes skill to navigate the tricky paths of communication. You mind the words, you mind the tone, you mind the extent of relationship you’re in. You want the person leaving the room feeling invigorated because he knows he’s done something valuable but also challenged enough to be better. Ultimately, as managers, it is a test of how good we are with people and seasoned managers don’t always succeed in this aspect.

Ruby on Rails creator wrote something interesting called trickle-down workaholism. I’d add to that and say, the effect is not just vertical,
it can also be outwards and lateral like a ripple. I remember colleagues chiding me from earlier years, “Your work hours make ours look bad. I feel guilty leaving the office on time because I see you and other people still glued to your screens.”

Celebrating busyness doesn’t just come in rewarding long hours. It can also be an unspoken work guilt; sneakier, definitely more manipulative.

My long slow crash came to an end after five years. Even as I joined my former bosses as a partner for a new venture (exciting, right?), inspiration often flickered. There wasn’t much to draw from the well to begin with. The dissatisfaction — and eventual disengagement — became even more pronounced when I did some traveling and reconnected with close friends.
My world expanded in ways that made me realize how little I was doing for myself (airport lounges make for effective spaces for introspection, mind you).

I often think about the circumstances during those busy years. Why didn’t we ever transition to working smart? When the projects tripled, the company hired more PMs, programmers and designers. The team grew but the problems seemed to have scaled as well. In hindsight, what fueled our creative energies back then — rapid growth — also became our downfall. In the midst of it all was a lack of calm, level-headed organizational leadership to quell the agitation around us. Eventually, the missteps became too many and the relations too strained. When one is occupied with potential earnings, who had the time to talk and reflect?

There’s a long list of hacks one can do in a bid to work smart; several productivity apps that promise to make life better. Advise that I feel only superficially glazes over what it really means to work smart — a continuous refining of processes, weeding out duplicates and unnecessary actions, eventually trimming down the steps. Refining achieved mainly through trial and error and knowledge gained.

How do you know which tasks have the biggest impact? Experience. How do you know putting as many new developers as you can on a project with a looming deadline doubles your to-do list instead of halving it? Experience. Working smart is about astute decisions guided mainly by intuition, guided by experience, guided by the many errors, all of which neatly wrapped in a bundle we call hard work. But this newly gained wisdom all goes out of the window when the vision is to move forward in the most rapid way possible. Full steam ahead. Sustainability, not speed, will give organizations a real chance for growth.

This article was written in 2017 and took a year to be concluded.

Rebekah Roque

Written by

tech life, film reflections, travel stories

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade